A Perfect Gift
by Piixiefawn
Summary: Simon has been dancing around his feelings for Jeanette for years. Can the holidays help bring them together? Simonette fluff with a sprinkle of angst. Hints of Theonore and Alvittney. Rated T for some language
1. A Walk Home

**Hi! If you're reading this, thank you. I want to say I started this fic as a joke and it some how turned into an actual full fledge fic. I've got 10 chapters for you that I wrote on my phone. So if there's any errors, let me know!**

 **I want to clarify that the universe for this fic is based off the 80s cartoon with some artistic liberties I took with their physical appearances.**

 **I hope you enjoy. I actually had fun writing this!**

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Winter break; it was the second most coveted time of year for those still attending school. As soon as the bell rang, the halls were flooded with students who had spent the week anticipating that very moment. At least, that's how it was for most.

Simon Seville was not most. He had remained behind in his physics class, droning on and on to his teacher about how he needed something, anything to do over the break to keep his brain from getting to lax. Teachers were used to students begging to not be given any work over the break, not begging to receive it.

" , please! I'll lose my mind if I'm cooped up with Alvin for two weeks with nothing to work on!" Simon leaned over the desk, urgency present in his steel colored eyes.

The teacher in question shook his head, his hand raising to pinch the point between his brow. "Simon, it's your junior year. You only have a couple of breaks left. You should take this time to enjoy it."

Simon's brows knitted together, frustration ever present in his features. "That's what everyone keeps telling me." He crosses his arms over his chest, gaze now downcast to the old oak of 's desk.

The older man smiled, placing a reassuring hand on the teen's shoulder. "Don't stress yourself out. Try to enjoy your time off. Goof off with your friends. Take a nap in the middle of the day. Just try to be young."

As Simon left the room, he had a sinking feeling begin to settle in his gut. _Friends_. Yeah, he had friends. But he was often treated as the punchline for jokes or used for his brains. There weren't many people he felt truly comfortable confiding in.

Even his own brothers. Theodore was kind enough. But it seemed the older they got and the more they participated in school activities, the less he saw of him. Then there was Alvin.

He often chastised him; branding him a 'nerd', telling him he was a 'buzzkill', reminding him that the more he droned on about 'science garble', the less people would want to be around him. Of course, Simon never really cared much for the company of those who looked down on intellect. Still, it didn't make it hurt any less.

Simon stepped into the brisk, December air. Sure, California didn't see snow very often and it was generally warm, but that didn't change the fact that it was an unusually chilly day. He breathed out, his breath visible in front of him, while the cold caused a fog to form over his glasses.

His hands rub together vigorously, a futile effort to warm the skin beneath his tan fur. He began to move forward, gusts of wind smacking his face, causing the dark hair on his head to swirl around chaotically.

Down the path a ways, Simon's eyes were caught by a figure, moving tentatively along the sidewalk outside of the library. She was huddled in close to herself, lithe limbs pulled tightly to her, while her nose was buried into the large scarf draped around her neck.

Simon broke into a sprint, trying to catch up to her. "Jeanette!" He rang, and arm waving somewhat frantically to try and catch her attention. The chipette stopped in her tracks, head turning to see who had called out to her.

She gave him a soft smile, returning his wave with a slight raise of her hand. After making it to her, Simon placed his hands on his knees, lurching over as he tried to catch his breath. "It really…..is cold…. out… huh?" He managed between huffs of air.

Jeanette laughed and nodded, "I-I don't think we've seen this kind of cold in a long time." A finger tapped thoughtfully at her chin for a moment, "I just can never seem to get warm."

Like Simon, Jeanette had been slender and seemingly fragile. That accompanied by their poor sleeping habits and tenancy to miss meals meant they physically weren't as equipped for harsher weather like their siblings. Simon usually toughed through it, knowing it was easy to simply bundle up or stay cooped up in a warm space.

Jeanette, on the other hand, would have to deal with the likes of the fashion conscious Brittany. Anytime Jeanette would attempt to bundle up to her liking, Brittany would demand that they 'had an image to uphold' and 'wearing all those baggy clothes would make her look frumpy'. Jeanette, on the other hand, never cared much about what others thought in regards to her appearance. Despite Brittany's persistence, she refused to go without a heavy jacket and a scarf on brisk days.

Simon took in her appearance, noting today must have been one of Brittany's victories, judging by Jeanette's pleated skirt. For the past couple of months the tallest chipette had solely worn jeans and sweaters. Simon's brow perch high and was accompanied by the shaking of his head. "What was her reasoning today?"

Jeanette looked at him, green eyes conveying confusion until she noted his gaze shifting to her skirt. She sighed, pulling her jacket tighter around herself. "W-well, we had to perform in drama class… a-and Brittany said we had to look 'cohesive'." Jeanette gave a couple of air quotes at the end.

Simon laughed "At least she knows the word 'cohesive'. I'm sure Alvin couldn't even pronounce it." The air rang with a unified chuckle between the two. "Where are Eleanor and Brittany, anyway?"

"O-oh, I had to go to the library for a little bit." That made sense. Simon looked to the watch on his wrist, noting it was already 4:30. He hadn't realized how much time he had spent after school.

The blue-clad chipmunk was thankful he had seen her. With the brisk weather and quickly setting sun, there was no reason for a teenage girl to be walking alone. The Miller's house was close enough to his own. It would be a breeze to drop her off and then head home.

Another gust of wind caught up to them, resulting in Jeanette hurriedly holding her skirt to keep it in place. The frustration on her face was now visible.

"Oh, here!" Simon quickly retrieve his bag from off his shoulder, pulling out the sweatpants that he had worn for gym class "we didn't really do anything today, so I promise they don't stink."

She happily took them and gave him her thanks. Jeanette slid the fabric over her slender legs and sighed in relief at the new warmth they provided her. "I can't thank you enough, Simon. I was really dreading walking home in this skirt."

Simon noted the way the fabric bunched up around her ankles. He hadn't realized how much taller he was than her now. As kids, Jeanette had always been just a tad taller than him. It wasn't until freshman year that he began to surpass her. Though she wasn't short by any means, Simon now seemed to tower over his group, gangly limbs and all.

They began their walk home, lacing it with conversations of past and upcoming projects, music, and life with their exuberant siblings. It was times like these when they would really come out of their shells. They were more than a couple of nerds. More than a clumsy, awkward girl and a know it all science nut.

Simon and Jeanette, despite being pushed to the back most of the time, were talented; filling the empty streets with tunes as they walked. Jeanette would bounce up and down or dance a little to their own made up tune. Simon would always be there to catch her when she tripped on her shoelaces or spun one too many times.

Their relationship was comfortable and uncomplicated. There was never conflict or confusion. It was easy. Simon never failed to have a good time with Jeanette. Aside from Theodore, she was the one person he felt truly safe around.

Simon found himself stealing glances at the shy chipette, noting the way her features would light up or how her cheeks flushed with the cool air. Then he began to feel it. It was something he had experienced a lot more lately. The way his heartbeat quickened.

This wasn't a recent event and the feelings weren't far and in between. It had been frequent for the last couple of years now. Her presence was refreshing and warm. Every moment he spent with her was too short. Every time she was close wasn't close enough.

It was only about a year ago that Simon had truly realized what he was feeling. It had happened around the time Alvin and Brittany started dating the first time. The pair had been fighting vigorously over the phone, resulting in Simon leaving the house and heading to the library to clear his head.

There he had found her. Jeanette was curled up in one of the reading nooks. Her knees were pulled tightly to her chest, while her green eyes were fixated on the pages in front of her. He had noted the way her pink frames had slid down the bridge of her nose.

He had been transfixed and content observing the focused chipette. It was that moment he realized what he had been feeling all that time. Every moment with her since was no different. Just like all the other times, his stomach felt fuzzy and his hands clammed up.

As they walked up to the front door of the Miller residence Simon felt himself dreading the inevitable goodbye. He swallowed a lump in his throat giving Jeanette a soft smile.

The chipette returned the gesture, about to turn towards her door before stopping and looking back to Simon. She reached for one of his hands and held it enthusiastically between her own two. "I forgot to tell you! Tickets to the science center are half off next week. I-if you're not busy would you…" Jeanette seemed to stumble, the confidence she had just displayed quickly faltering. "Umm…"

He knew she was shy. No matter how close they were or how much time they spent with one another, she still had moments where he could see her anxiety bubbling to the surface. Simon just smiled a bit brighter and nodded. "I'd love to." Came his simple reply.

She was grinning now, larger than he had seen in a long time. "Oh good! How about Monday?"

"Monday sounds perfect." Simon agreed.

Jeanette headed toward the door, opening it and then looking to Simon over her shoulder. "Great! It's a date." After speaking she slipped inside, leaving Simon behind and a bit dumbfounded.

 _….. 'A…. Date?'_


	2. Nerves

_Thump. Thump. Thump. Thump._

Theodore looked up to the ceiling, his brow raising in frustration as he heard, what sounded like, frantic pacing in the room above him. The boys had been given their own rooms a while ago: Theodore into Dave's old office, Alvin had converted the basement into a 'man cave', and Simon had stayed in the room they all once shared.

The youngest of the brothers had assumed noise would never be an issue. Simon was the quietest of the three, with the exception of an occasional science experiment gone wrong or when he would practice with any of the various instruments he owned.

None of that ever bothered Theodore. But it was two in the morning and this was not the time for this sort of thing.

Theodore climbed out of bed, his eyes droopy while his face conveyed a certain level of annoyance that was usually only demonstrated by Simon himself. He reluctantly made his way up the stairs and headed straight to the source of the racket.

Not bothering to knock, Theodore opened the door, taking immediate note that the tallest brother was, in fact, pacing anxiously back and forth.

Simon's room was normally clean to the point of feeling eerie. In its current state, it looked more like it could be Alvin's. Articles of clothing and books were strewn about the floor. His laptop teetered dangerously on the edge of his bed. All the while, Simons silvery eyes were glued to his cell phone, held by shaky hands.

Theodore blinked a few times, his eyes adjusting to the light in the room. Then his face contorted into one of concern. "Simon, what are you doing?"

He halted in his tracks instantly, his gaze now falling on his brother who he hadn't even heard enter the room. "I...uhhh… was wondering if it was too late to text someone."

"Si, it's two in the morning," Theodore started, "it's too late."

Simon's shoulders slumped, while the palm of his hand connect to his forehead with a _smack!_ "Of course it is, what the fuck was I thinking?"

Theodore took in his brothers appearance, noting the way the deep brown hair on his head fluffed up, or the slight flushing of his cheeks beneath his fur. "You wanna tell me what's going on?" He asked in a gentle tone.

The shorter of the two made his way over to Simon's bed, moving his laptop and sitting down. He was then met with the teen in question throwing himself down next to him, immediately fixating his eyes on the ceiling. "Jeanette asked me to go to the science center with her." He said flatly.

Theodore's brows knit together in confusion. "So? You guys go there all the time. What's the issue?"

Simon's chest rose and fell as he let out a heavy sigh. "I know that! It's just…" he trailed off, not entirely sure how to put his feelings into words.

Then it clicked. Theodore's ears perked up high on his head while his mouth gaped slightly. "You mean like a date?!"

"That's the thing, I don't know if that's what she meant!" He shot up, his hands beginning to move frantically as he spoke, "she said 'it's a date!', but she could have meant that as just an expression, y'know how people do that, or she could have meant it as 'it's a _**date**_ '." He added emphasis to the last word, hoping it would properly convey to Theodore what he was trying to say.

Despite Simon's 'superior' intellect, his brothers always seemed to have better luck with girls. He was hopeless and completely oblivious to any sort of advances or flirting that came his was. Alvin had a number of relationships, including his on again, off again train wreck with Brittany. Even the youngest of the three brothers had been going steady with Eleanor for the past seven months.

In reality, Theodore probably understood girls better than his older brothers ever would. He was receptive to feelings and unabashedly kind. He was the perfect person to talk to in this situation; that is, if Simon could figure out how to articulate his feelings properly.

"Do you not want to go on a date with Jeanette?" Theodore asked. While his brother had never outwardly said it, they all assumed he had feelings for the dark haired chipette. It was possible they could have been wrong all along.

"N-no! Of course I do! She's… well she's just…" his eyes seemed to glaze over, as thoughts of the residential 'clumsy nerd girl' race through his head. "...Magnificent."

"I'm still not seeing the problem here." Theodore interjected. His brows knitted together tightly, green eyes narrowing at his dazed brother. Man he was weird when it came to romance.

"I don't want to read too much into it, Theo." Simon began to explain. "What if she didn't actually mean it as a date date and I make it weird and I ruin our friendship."

"Do you want me to have Eleanor ask her what she meant?" Theodore offered. Alvin had asked the same of Brittany when Theodore was confused about Eleanor's feelings towards him. It only made sense to repay the cosmic favor.

"No!" Simon immediately bit back, anxiety now returning to his features. "I-I don't want her to feel any sort of pressure or anything."

Theodore rolled his eyes. "She's going to be more aloof than that, Simon." He stated flatly. Since when did he have to be the voice of reason for the voice of reason? "I'll just see if she can gently coax it out of her without directly asking. Is that okay?"

Simon thought on it for a minute. He didn't like scheming. Ever. And it was rare any sort of little plans came from Theodore. As opposed to Alvin, however, Theodore's ideas were only ever about helping others. Not self gain. Simon hung his head somewhat bashfully and nodded. "I would appreciate that."

Theodore smiled, placing both hands on his brothers shoulders. "Okay. I'll talk to Eleanor in the morning." Simon nodded his understanding. "And simon," he began, drawing his brothers gaze to his face, "please stop pacing and go to sleep."


	3. Sisters

It wasn't uncommon for the Miller hour to be swirling with the scent of freshly baked goods. Nine in the morning and Eleanor was already working diligently to craft a delicious breakfast for her sisters and guardian.

Her brown eyes shifted from the French toast she had made, over to the bacon she knew only would eat. She smiled proudly. The chipette wasn't one to toot her own horn, but this may have been some of her best work yet.

The blonde was drawn out of her adoration at the sound of her phone ringing. Her grin spread wider when she took note of the caller ID and she was quick to pick up. "Hi Theo~" she sang out pleasantly.

"Hi Ellie, how's your morning going?"

"Fantastic! I just made the best breakfast. You should come eat with us!"

"You know I would, but Dave made breakfast and I don't want to hurt his feelings."

A unanimous chuckle rose between the two voice. "That's okay! So what's up?"

"Well I kind of had a favor to ask you…"

Eleanor's interest was now piqued. Theodore didn't ever really ask for much very often. His tone sounded serious and that was enough of a cause for concern. "Sure, what is it?"

"I-it's about Simon and Jeanette."

Simon and Jeanette? Her sister had seemed fine the night before, so if the two had some sort of issue, she certainly didn't show it. "What's wrong?"

"Nothing's wrong! Just… different… I think."

"Oookay…" Eleanor continued to listen, hoping for some more clarity.

"Well, Jeanette asked Simon to go to the science center on Monday…"

Eleanor's brows knitted together in confusion. "You're losing me Theo. What's so different about that?"

"Well after Simon said yes, Jeanette told him 'it's a date'."

Eleanor's expression now shifted to one of surprise. "No way! She asked him out?" Jeanette had never been very assertive. She had always assumed when the pair did finally decide to move their relationship to a different level, it would be Simon making the first move.

"That's the thing. He doesn't know if she meant it as just an expression, or an actual date." Now that made more sense.

Jeanette was clumsy, not only in a physical sense, but in a verbal one. She wasn't always the best at conveying things. Even Simon, who understood her better than most, was not exempt from the occasional confusion.

"Oh no. He's probably losing his mind over this, isn't he?"

Theodore responded with a simple "mhmm."

"So what does this have to do with me?" Eleanor asked, still not fully understanding the situation.

"I was wondering if you could kind of… gently prod her to figure it out? I know Brittany would probably be too blunt about it."

Eleanor smiled. "Of course. Let me see what I can do."

"Thanks Ellie! You're the best!"

"Anytime! I'll talk to you later then?"

"Yup! I love you." Everytime he said that Eleanor was reminded of the warm, fuzzy feeling he never ceased to give her.

"I love you too! Bye bye!"

"Bye!"

After hanging up the phone, Eleanor went back to finishing breakfast, all the while trying to think of a way to get the needed information out of Jeanette. Then it hit her.

'Isn't Monday Christmas Eve?'

After a casual breakfast around the kitchen table and some much needed cleaning up, the residents of the Miller house all dispersed. went off to take a small nap, Brittany went to the store, insisting she needed a new outfit for a Christmas Eve party she had to attend, and Eleanor left the kitchen to go find where her sister had run off to.

She wasn't hard to find. Eleanor found Jeanette in the living room, curled up on the sofa with her nose buried in some novel. She made her way over, pulling back the blanket the taller chipette was snuggled in and climbed underneath with her.

"What're you reading today?" Eleanor prompted. This resulted in Jeanette quickly closing the book and placing it cover down on her lap.

"I-it's nothing. Just… something I picked up at the library." Eleanor knew that response well. It usually meant she was reading some sappy romance that she was too embarrassed to talk about.

Eleanor decided to disregard the topic of the book for now. "I wonder what Brittany's gonna end up buying for her party on Monday." She figured bringing up the day itself was the perfect way to naturally integrate into this conversation.

Jeanette seemed to freeze. She blinked a few times, her face quickly flushing. "W-wait… Christmas Eve is on...Monday?"

"Yeah. You didn't know?" Eleanor wasn't too surprised that it had slipped Jeanette's mind. She had a tenancy to be a bit of a scatterbrain from time to time and the year had flown by so fast.

Jeanette buried her face in her hands, whining softly. "I'm so inconsiderate. I didn't realize."

"Woah! What's wrong Jean?" Eleanor wrapped her arms around her sister, attempting to quell her obvious anxiety.

"I asked Simon to go to the science center with me on Monday. I don't want to take up his holiday." Jeanette pressed her face into her sisters shoulder, embarrassment overcoming her. "No wonder the tickets are half price."

"I'm sure he knows! He wouldn't say yes if he didn't want to spend time with you." Eleanor gently rubbed her sisters back, the action soothing her almost instantly.

Eleanor had to think quickly. This had shifted from a mission for information, to calming her anxious sister. "Besides, Christmas Eve is pretty romantic, don't you think?"

Jeanette's head shot up, her face flushing deeply and green eyes going wide. "R-romantic?"

Eleanor felt a bit of a sting. Maybe Jeanette didn't intend for it to be a date after all. "Oh, I'm sorry. I just assumed it was a date…"

"N-no I mean-!" Jeanette began, but quickly pressed her lips into a flat line as she thought about the night before. "I didn't… it doesn't have to be a date. I just… I left it kind of...open."

"What do you mean 'open'?" Eleanor asked.

"W-well… if he doesn't think of me like that…" her head dropped, strands of brown hair falling in her reddened face, "I don't want to make things weird…"

Eleanor was dumbfounded. How could these two be so oblivious to one another? It was obvious to anyone with eyes that they adored each other, yet they were both panicking and putting up barriers to protect themselves from potential pain.

The younger of the two wanted so desperately to grab her sister's shoulders and shake her. But she knew better. Jeanette was soft and sensitive. She had been hurt before and Eleanor understood her hesitation. "Jeanette, Simon cares about how you feel. I don't think anything you say or do will make things weird."

Jeanette's lower lip poked out, trembling slightly as she held back anxious tears. But she nodded nonetheless.

"You like him a lot, right?" Eleanor earned another nod. "Then just be yourself and go have fun at the science center. Don't think about it too hard." She punctuated her sentiment by gently poking at Jeanette's head, eliciting a laugh from her.

"You're right Ellie. Thank you." The older chipette smiled warmly at her little sister. Most would find getting advice from your younger sibling to be a bit embarrassing, but Jeanette never felt that was. Eleanor was mature and caring. She was intuitive to the emotions of others in a way that most couldn't begin to comprehend.

"I'll let you get back to your book now." Eleanor gave her sister and gentle peck on the forehead before taking her leave. After slipping away and into her own room, she pulled out her phone and dialed Theodore.

After swapping pleasantries and discussing the info they both had on Simon and Jeanette, Theodore was left asking what they should do. Eleanor didn't hesitate. She had made up her mind halfway through her conversation with Jeanette. "They need to sort this out themselves. They'll come together when they feel like it's right."


	4. Brothers

"Sorry Simon, Ellie couldn't get anything out of Jeanette." Theodore said apologetically. He wasn't good at lying and never had been. He hoped this one was small enough for him to get away with.

Eleanor and Theodore has promised one another they weren't going to meddle in this situation. Simon and Jeanette had been dancing around this topic for years and it was time everyone let the pair of them work it out together.

"That's alright, Theo." Simon replied, giving his little brother a small smile. Jeanette had a tenancy to be a bit oblivious and spoke in circles. It wasn't surprising Eleanor couldn't get a straight answer from her. Simon just laughed. It was one of those little quirks about her that he found so fascinating.

"Y'know Simon," Theodore began, taking a seat next to his brother on the couch and nudging him, "If you like Jeanette, you could just tell her."

"I've tried. It's just…" Simon swallowed hard, his eyes falling into his lap, " whenever I even get close my throat swells up and my mouth get dry. Then I feel like I'm gonna die."

"And I thought Alvin was the dramatic one…" Theodore drawled out, earning an eye roll from the other chipmunk. "You never know if you don't try, Simon. The worst that can happen is she'll say no."

"No, The worst that can happen is it'll destroy our entire friendship." Simon said flatly. "Jeanette's has boyfriends before. I'd be stupid to think I stood a chance."

"Yeah, dumb jocks Brittany's set her up with. Has she ever seemed happy in those relationships?" Theodore never liked to see the people he cared about feeling down about themselves. However, there was only so much he could say or do in this situation.

Simon had remained quiet for the most part, before slinking back upstairs after a long, uncomfortable silence. Closing the door behind him, he immediately went to his desk, sitting down and sliding open one of the drawers.

Inside this drawer was a number of writing utensils, paper clips, and other mundane supplies. But against the dull contents was a flash of bright purple. A rectangular box that he had been hiding away for months.

Simon plucked it out of the drawer, opening the box to peek at what was inside. A round opal, with two silver rings around it and a small star charm hanging from the end opposite of the chain.

He had seen her eyeing this same necklace on the multiple trips they had taken to the mall. Without fail, she always found an excuse to walk by the small jewelry store just to look at it. When it finally sold, she sighed with a bit of disappointment, unaware that Simon had been the one to buy it.

He knew it would be the perfect Christmas gift for her, and after saving up enough money from his part time job at the library, he was finally able to afford it.

Simon was pulled from his thoughts at the sound of his bedroom door slamming open. Without any time to react, he was knocked out of his chair by a quick moving brown and red mass. "What the fuck?!"

"Whaddya mean 'what the fuck'?!" Alvin replied, pushing his brother down against the ground with all his might. The taller of the two presses his hand against Alvin's face in an attempt to shove him off. "You're here sulking in your room like a big baby!"

"I'm not sulking you maniac!" Simon retorted. He continued to slap and push against Alvin, cursing his thin limbs all the while. "Get off me, Alvin!"

"Not until you stop treating yourself like shit!" Alvin yelled, gripping his brothers shirt tightly. Simon halted, looking at Alvin's furious expression.

"What the hell are you talking about?!"

Alvin's hold on Simon's shirt only tightened. "Theo told me you've got some weird 'maybe' date with Jeanette and now you're all boohooing 'cause you don't think you're good enough."

"Theodore…" Simon growled out begrudgingly. Alvin was the last person he wanted to know about his situation. Yet here he was, pinned to the floor and being given the most aggressive pep talk of his life.

"Don't be mad at Theodore. He just doesn't know how to handle your dumbass like I do." Simon's eyes darted off to the side, refusing to look Alvin in the eye. "Why are you getting so worked up? It's just Jeanette."

"It's not _just_ Jeanette!" Simon spat, now looking harshly at Alvin. "She's...she's…"

"Yeah, yeah. I know," Alvin rolled his eyes, "you two have been all 'goo goo eyes' since sixth grade."

"W-we have not!" Came Simon's rebuttal. He made another attempt to push Alvin off of him, but found it to be futile. He hated that Alvin was so athletically inclined.

"Yes you have! Anyone with eyes has noticed!" Alvin pushed back, causing Simon's head to thump against the floorboards. "If you don't take chances you're gonna regret it!"

"You don't think I know that?!" Simon managed to move his leg up, his knee hitting Alvin in the abdomen and sending him backwards onto his rear.

Alvin heaved, the wind knocked right out of him. Simon stood, looking down at his infuriating brother with a raised brow. Moments later, he was taken aback at the sound of Alvin cackling. "M-man Si! You're sneaky!"

Simon couldn't help but chuckle a bit himself. "Did you forget I have legs?"

"Kinda, Yeah!" Alvin admitted. Upon regaining his composure, he rose from the ground and walked over to Simon's bed to take a seat. The more boisterous of the two then patted at the spot next to him, wiggling his brow and beckoning his brother over.

Simon sighed, reluctantly plopping down next to Alvin. All the while, the red-clad chipmunk wore a large smirk, excited to try and give his 'know-it-all' brother some advice. "Girls are confusing, Simon. Trust me I would know."

They both laughed, nodding at the sentiment. "Yeah, they really are." Simon admitted.

"Take Brittany for example. One second she wants to spend every hour of every day with me. The next second, she doesn't want anything to do with me. It just depends on what mood she's in." Alvin shrugged at the end of his sentence, while Simon nodded along.

"I don't see how that relates to Jeanette…" Simon began, chewing on the inside of his cheek as he thought. "Brittany and Jeanette are complete opposites, actually."

"Exactly!" Alvin agreed. He held up a finger and pointed between the two of them. "You and I are also opposites." Simon looked confused, his brows scrunching tightly together. Alvin sighed out his response. "Brittany and I have a lot of issues. We have since we were kids. But that's because we both feel a need to be in control. I can handle her and I adore her anyway."

Simon bit back from asking once again how Alvin's situation related to his own. He was sure at this point Alvin must have been building up to something.

"Brittany and I have always taken a lot of work, even as friends. But that's just who we are," he began and then settled on poking a finger into Simon's chest, "you and Jeanette, on the other hand, have always been so natural. So stop stressing so much. Just be yourself and this shit will fall into place."

Alvin was grinning now, wider that Simon had ever seen. The bespectacled chipmunk, on the other hand, couldn't hold back an expression of shock. Alvin...actually made sense for once? "You're right." He conceded.

"Damn right I'm right!" Alvin sing-songed out. "Take it from the love doctor, just be yourself and show that nerd girl how you feel. She's bound to fall head over heels for you." His brows danced around, resulting in Simon punching him in the arm to make him stop.

"I hate to say it, but, thanks Alvin." Simon smiled a bit.

"You're welcome, bro." Alvin looked from his brother, then around to the trashed room that only seemed to have become more of a wasteland after their altercation. "Jeez, Si. I've never seen your room so trashed." Simon only glared in response. Alvin then pointed to the little purple box on the floor, "what's that?"

Simon shot up, diving for the gift that must have been flung out of his hands in the crossfire. "It's how I'm gonna show that _amazing_ girl how I feel."


	5. Christmas Time

_"_ _Christmas, Christmas time is near,_

 _Time for toys, and time for cheer…"_

Simon opened his silvery eyes at the sound of a familiar tune. He sat up in bed, noting it wasn't coming from the radio on his nightstand (as it often had around this time of year). He pulled back his blankets, deciding to head downstairs to investigate the noise.

 _"_ _Want a plane that loops the loop,_

 _Me, I want a hula hoop…"_

Peeking his head around the corner and looking into the kitchen, the source quickly became clear. Alvin spun around the kitchen, singing the melody as loudly as he could manage. Theodore came in on the harmony, while his main focus was on a tray of cookies he was slaving over.

The song didn't sound like it used to. Their voices had changed with age, and while they were still higher than most, it was noticeable. It had seemed a lot changed with age as of late. But one thing always remained a constant in the Seville house; they loved Christmas.

Simon laughed a bit to himself, before deciding it was only fitting to join his brothers. It was Christmas Eve after all.

 _"_ _We can hardly stand the wait,_

 _Please Christmas don't be late"_

Alvin and Theodore turned to the new addition to the room, both smiling at Simon. "You seem like you're feeling better." Theodore noted.

Simon nodded and took a quick glance at Alvin who wore nothing less that a smug expression. Simon wasn't to keen on announcing to the world that a conversation with Alvin actually made him feel better. So he responded with a simple "Yeah I am."

Alvin walked over to Simon, placing his hands on his brother's shoulders and staring him in the face. "Remember, it's just Jeanette. Don't overthink it."

He then dropped his hands and quickly left in a gust. "Where are you going Alvin?!" Theodore shouted after him.

"This is the first Christmas Eve we haven't had to perform in a while!" Came his response from somewhere else in the house, "I've still gotta get Brittany a present before the party tonight!"

Theodore and Simon both shook their heads in response. "Waiting till the last minute… some things don't change." Simon sighed out. He then looked to the cookies Theodore was diligently working over. "Are these for Eleanor?"

The younger brother smiled brightly and nodded, "We agreed to make each other presents this year." That wasn't so different than any other year. The pair were masters in the kitchen and if Simon had Theodore's culinary skills, he would opt to do the same. "I heard about the necklace."

Simons face quickly flushed and his eyes darted in the direction Alvin disappeared off to. "Alvin…"

"I-I'm sorry I told him about everything… I just didn't know what to do." Theodore's face dropped and Simon felt a twinge of pain for his remorseful expression.

"It's alright, Theo." He started, walking over and patting him on the back. "He did… help… as much as I hate to admit it."

"I wonder what Jeanette got for you…" Theodore trailed off, his expression shifting in thought.

"She doesn't know I was getting her something, so I wouldn't assume she got me anything." Simon said with a shrug.

"Eleanor said-" Theodore immediately stopped himself, slapping his hand over his mouth. His green eyes darted around. "Never mind."

"What did Eleanor say?" Simon asked, his eyebrows raised high in curiosity.

Theodore sighed, knowing that this wasn't something Simon would want to just let go of. "W-well… when I talked to her this morning she said she spent an hour getting tape out of Jeanette's hair because she was up all night trying to wrap a present she really needed for today."

This seemed to be a satisfying enough response for Simon. He hummed his approval lightly. It wasn't unusual for friends to get each other gifts. They had done it before, but usually they asked what the other wanted or even if they wanted to exchange gifts. Something about her wanting to surprise him with something made his heart beat a bit faster.

"What time are you supposed to go to the science center, anyway?" Theodore asked, his head cocking to one side.

Simon's eyes widened, having gotten up without putting on his glasses or checking the time. He squinted at the clock on the wall, but to his dismay was unable to read it. "Quick, what time is it?!"

Theodore looked to the wall and then back to Simon, "Ten Thirty-six." Theodore said, a bit nonchalant. The taller chipmunk could kick himself for sleeping in so late. This is what he got for not going to bed at a decent hour.

"I'm supposed to meet her at the bus stop at noon and I haven't even showered yet!" In the same fashion Alvin had, Simon quickly scurried away, his feet vigorously thumping up the stairs.

He made quick work of showering, only taking about fifteen minutes. However, it was deciding what to wear that would be the hard part. Simon was not a fashion conscious individual and Alvin often made comments about what a 'tragedy' his closet was.

After a good forty-five minutes of trying things on and then tossing them on the floor, he settled on a blue striped sweater with a white button up beneath it. Simon decided a simple pair of jeans and his usual red converse would suffice. He didn't want to appear as though he were trying too hard. After all, as Alvin pointed out, it's just Jeanette.

With roughly twenty minutes to spare, he triumphantly walked down the stairs to ask for Theodore's opinion on his attire. Not finding him anywhere in sight, Simon pulled his phone from his pocket, taking notice of a text on the screen.

Theo: Heading over to Eleanor's. Have fun at the science center (:

He sighed, shaking his head. Simon patted down his pockets, ensuring he had everything he would need for the day.

The chipmunk then heard footsteps descending the stairs. Turning his head in the direction of the noise, he saw Dave, stretching his arms out and yawning.

"Did you just wake up?" Simon asked with a small laugh.

Dave shook his head, holding up a stack of papers in his hand. "No. I've been working on a song all morning." Of course. Dave wrote some of his best songs around this time of year. He assumed this one would be no different. "Where are you off to?"

"The science center." Simon said.

Dave smiled, something in his expression bittersweet. "You fellas sure are growing up fast." Simon returned the small smile and nodded. "I take it Alvin and Theodore already left?"

Another nod from Simon. "Theodore went to see Eleanor and Alvin forgot to get Brittany a gift."

This elicited a laugh from Dave. "I invited and the girls over for Christmas dinner tomorrow. Make sure to tell Jeanette in case she forgets."

"Will do." Simon looked to his watch and then back to Dave. "I should get going. I'll be home tonight."

Dave waved to his son and began to head into the kitchen, Simon assuming for a cup of coffee. "Remember, the buses stop running at ten. If you need a ride give me a call."

"Thanks Dave!" And with that, he was out the door. It would only take five minutes to get to the bus stop. Being that it was already twelve forty-eight, Simon began to worry Jeanette would get there before him.


	6. Tourist Season

Unlike before, today was a bit warmer, leaving the tallest of the chipmunks to begin questioning his jacket. It was too late now. He was already too far from his house to turn back and drop it off.

Simon felt immediate relief, spotting a familiar figure halfway down the road. He broke into a sprint, quickly catching up to the slender chipette. She stopped, turning to look at her now panting companion. "Y-you know you don't have to run…" she pointed out. "I would have waited for you."

He was bent over, much in the same manner he had been a few days prior, desperately attempting in catch his breath. "I don't… know why… I… didn't think… of that." He spoke between pants.

Jeanette laughed, light and bell-like. His heart skipped a beat. There it was again. Without fail, there was a fuzzy feeling present in his stomach, his hands becoming clammy, while he was sure his face flushed from more than just the run over.

Simon took in her appearance; a purple jacket layered over a white, knit sweater that reached her mid thighs. Her legs were covered with a pair of leggings, while she kept with her usual slouchy socks and sneakers. The one difference he really noticed was her hair. She seemingly dismissed her signature bun for the day, the top half of her hair being pulled back with a ribbon while the rest of it cascaded down her back in waves.

 _Had her hair always been so long?_

After a few more moments, they began to head to the bus stop together. Jeanette reached out, grabbing for Simon's hand. His heart pounded rapidly, but he made it a point not read too much into it. After all, they had held hands since they were kids; whether it be Jeanette trying to stable herself, an attempt to stick together in a large crowd, or simply because it felt right.

He welcomed the contact nonetheless, giving her hand a gentle squeeze, while her thumb rubbed absently over his own. The walk was quiet, something a bit different hanging in the air between the two. It was still a comfortable silence, as it always had been.

The bus seemed to pull up just as they arrived. The pair found seats quickly, Simon allowing Jeanette to sit closest to the window. Murmurs could be heard and eyes often shifted to look at them.

Simon swallowed hard. It wasn't unusual for them to be recognized in public; after all, how many singing, anthropomorphic chipmunks were there?

What they hadn't taken into consideration were holiday tourists. Sunny Southern California was a hot spot for those looking to escape the winter snow. Sure, they loved to perform and Alvin and Brittany loved the attention, but when it came to the other four in the group, there were times they would have rather flown under the radar. This was one of those times.

There was a flash from a camera and Simon's face quickly contorted into a scowl. He turned to Jeanette, who seemingly hadn't been paying much mind to those around them. Instead her green eyes stared out the window, watching the buildings and people as they went by. Simon leaned in close, tapping her on the shoulder.

"Put your hood up." He whispered. She was pulled from her dazed state and was now aware of their surroundings. Her response was a small "oh!" And she flipped her hood up quickly. Simon did the same, one of his hands then sinking deep into the pocket of his jacket, the other still holding Jeanette's hand tightly.

Their faces remained turned toward the window, hoping this would hinder anyone from taking pictures. "We got recognized a lot less when we were younger." Jeanette pointed out.

Simon nodded. "Teenagers are more interesting, I guess. Especially when there's no guardian to ward off fans and paparazzi."

They knew this wouldn't be a huge issue at the science center. California natives were so used to seeing the chipmunks out and about, they never really bothered them. As for the tourists, when you're in the land of the rich as famous, you rarely decide to go spend your vacation in a place you weren't very likely to see many celebrities.

Throughout the ride, many people came and went. When it came time for them to exit, only a couple of other people got off the bus. They kept their heads down, Simon pressing a hand against Jeanette's back in an attempt to keep her close and prevent a potential stumble.

After making it off the bus and away from the peering eyes of tourists, Simon pulled his hood down, shaking out his dark hair. His gaze was then caught by Jeanette's feet. Her shoelaces had come untied at some point.

Simon gave a breathy laugh. He made quick work of kneeling down and taking the laces between his fingers to begin tying them. Jeanette's face quickly flushed. "I-I didn't notice…"

"It's alright." Simon reassured her. "I've got your back." The chipette truly had horrendous depth perception. One wrong move and an untied lace would result in a nasty accident. He gave the laces one last tug to ensure that wouldn't happen. "There. All done."

He stood up, now met with a gentle smile from his meek companion. "Thank you." She breathes out softly.

Jeanette's words seemed to fall on deaf ears. Simon hadn't responded, only stared at the deep emerald eyes that looked back at him. Her eyes were the most amazing thing about her. Brittany had a pair of sparkly blues, Eleanor, a deep chocolate brown. Somehow Jeanette had been gifted with a beautiful green.

Brittany had always been regarded as 'the pretty one', but in Simon's eyes, Jeanette was a true beauty. She possessed large eyes, that held a curiosity and wonder for everything around her. Her soft, delicate features and slender build weren't 'preferable' by today's standards, but he found everything about her captivating.

Simon was pulled out of his daze with a gentle squeezing at his hand. "A-are you alright, Simon?" Jeanette asked, her head cocking curiously to one side.

"O-oh! Y-yeah… sorry… just… lost in thought." Had it been Alvin, he would have said something slick. Theodore? Something sweet. But Simon wasn't any of those things. He was awkward and literal. No matter how much he wanted to tell her how captivating her gaze truly was, a crippling fear of rejection quickly outweighed any desire he had.

Simon cleared his throat and turned his gaze towards the science center. "Well, shall we?" he gestured towards the large building. Jeanette smiled and nodded, the two headed forward.


	7. The Science Center

Once inside the Science Center, Simon's nerves seemingly dissipated. It was a quirky little haven for them. The pair buzzed about, taking long amounts of time examining exhibits that most moved on from after a few short minutes.

Though they had probably seen each of these exhibits at least a dozen times over, they always treated them like they were new and sparkly, searching for things they may not have noticed before.

Simon was partial to the air and space exhibits. Though it was an additional cost, he always had to take the time to bounce around in the zero gravity harness. Space was his dream, after all. Currently, it was the closest he could get to it.

Jeanette held his jacket while Simon bounced around gleefully. Her lips turned into a smile at his bright expression. Alvin has often regarded Simon as having 'chronic bitch face'. But people never got to see him in these moments; mouth wide with a goofy grin, dark messy hair rustling around his face and ears, glasses slightly crooked from movement, and him not caring to fix them. The dark haired chipette felt nothing but pure adoration for him.

After his ten minutes was up, he made his way back over to Jeanette, face flushing slightly from embarrassment. Simon knew she wasn't judging him. She never did. Yet a part of him still felt a little silly for taking so much joy in something so simple.

"Did you have fun?" Jeanette asked. Simon nodded, his grin still present on his face. Jeanette smiles brightly in return. "I'm glad!"

"What do you want to do next?" He asked. He had an idea of what she was going to say.

"Could we go to the ecosystems exhibit?" She asked. It was always her favorite part of the science center and Simon was more than happy to oblige.

"Of course we can." This time it was him taking her hand and leading her towards the exhibits in question. His steel colored eyes would occasionally peer over at her, noting the warm, happy expression on her face.

While at the ecosystems, Jeanette spent most of her time bouncing on her heels, pressed excitedly against the glass, or pointing at things and rambling on about them. He'd seen it and heard it all before, but he never missed an opportunity to see her so excited.

Then they came to her favorite part of the exhibit; the kelp forest. It was a large, tunnel like aquarium, with schools of fish circling around them and large kelp towering over their heads. The chipette squealed with excitement, listing off the types of fish and stating the names she had given each one after her many visits. Simon listened to her every word intently, making sure to memorize everything.

Jeanette's green eyes were so focused on every little detail, while her hands pressed against the cool glass. He wanted to take in everything about her in that moment; her soft expression, her eyes that held nothing but wonder and admiration, and her tail, which flicked back and forth contently. Then he noticed a lock of hair which had fallen in her face and he resisted to urge to push it out of the way.

Instead, he shoved his hands in his pockets, now remembering the small box he had tucked away to give her. His face flushed suddenly, not sure if this would be the best time to give it to her or not. It was her favorite place, but he would hate to distract her for even a second. He finally decided he would hold off and give it to her later.

Simon's attention was drawn back to Jeanette, knowing she had said something but having been too lost in his thoughts to hear it. He shook his head, brown tresses fluffing up. "I'm sorry, what did you say?"

"They just opened the King Tut exhibit. Should we go see it?" She asked. Simon nodded excitedly. He had completely forgotten about the recent addition to the science center. He and Jeanette has buzzed about it for months and hadn't yet had the opportunity to go see it.

While this particular exhibit was truly something to behold, it didn't seem to hold the attention of most. Simon and Jeanette, however, remained there for a lengthy amount of time, swapping facts and theories about ancient Egypt.

This exhibition was also an additional fee, but to the pair of enthusiastic chipmunks, it was well worth the cost. Being able to see genuine artifacts from an ancient tomb had them buzzing with joy.

They must have spent at least an hour in that particular part of the science center. Simon had been staring at a few artifacts when he felt a soft tap on his shoulder. He turned to Jeanette, noting a somewhat nervous expression on her face. "What's wrong?

"O-oh nothing. I was gonna ask if you wanted to get something to eat. I'm a little hungry." He took note of the pink in her face, barely visible beneath the tan fur. He felt bad for not having thought about food earlier. Simon flipped his wrist, looking at his watch and noticing it was already five o'clock.

"Oh it is late. The Science Center will be closing soon." Like it had been listening to the conversation, his stomach emitted a load growl, causing his cheeks to redden. "Yeah we should probably eat…"

They hadn't seen everything there was to offer, but it didn't matter to them. They were just things to look forward to on their next visit.

Once more the pair walked hand in hand, leaving the science center behind and searching for a good place to eat. Christmas Eve in Los Angeles was bound to be busy. Many restaurants would be busy hosting parties or tending to those who didn't feel like staying home for the evening. Simon chewed on the inside of his cheek, trying to spot anywhere that didn't seem too busy.

Simon spotted a small Italian restaurant called 'Bella's' that he remembered Dave raving about a while back. It was a bit of a long shot, but it couldn't heard to peek in and take a look. He knew a nice meal would put a significant dent in his wallet, but he didn't work all of those hours at the library for nothing.

"How about Italian food?" He asked her, pointing to the building with its patio dining. Despite the seventy-five degree weather, the clouds overhead held the looming threat of rain. Dining outside certainly would have been nice, but he supposed it was best saved for another time.

Jeanette nodded. "That sounds good~" she practically sang. This made Simon's heart flutter. The paired walked inside, immediately taking in the atmosphere. There were high ceilings, string lights, and white linen tablecloths. The dining room was full of people buzzing about and enjoying their meals. Against the largest wall was a small stage with a band. It was beautiful, and very clearly a venue meant for a date, not a couple of friends.

Simon's lips pulled into a tight line, not sure how his companion would take this. However, this could be some sort of cosmic push from the universe. Maybe it was the perfect situation to find out if this was truly a date or not. After all, the waiting line wasn't too long and it certainly did smell good.

He looked to Jeanette, trying to read her expression. She appeared content enough, which eased his concerns. Simon took a page from Alvin's book, and decided to play the situation off cooley. "This place looks really nice." Jeanette said, a bit of awe lacing her tone.

"It really does." Simon replied.

They had taken a seat on the cushioned bench, waiting patiently to be seated. A couple of people here and there recognized them, greeting them softly or simply waving. Simon always preferred these kinds of people. They were considerate and managed to remain unintrusive. They pair would return the gestures, not wanting to be rude.

"You think we'd be used to this by now." Jeanette laughed.

Simon shook his head. "I don't think it ever stops being weird."

It was a few moments later when a hostess walked up to them. "Hi guys, just two of you?" She wore all black with her blonde hair pulled into a tight ponytail, with a large, welcoming smile. He was sure it was a smile that had been perfected after long hours of seating infatuated lovebirds. Then realization seemed to strike her, "Oh! I know you guys! You're The Chipmunks!"

Simon rubbed the back of his neck, with an awkward grin, while jeanette simply fidgeted with her hands and sheepishly laughed. "Yeah that's us." Simon spoke, not quite sure whether he should look at Jeanette or the hostess. "D-do you think we could sit somewhere…a little…private?" he asked, trying to not sound rude.

"O-oh of course!" She grabbed a couple of menus, directing the pair to follow. "We've got just the spot for celebrities who want to 'lay low'." she mused. Simon hated being thought of as a celebrity, but he couldn't blame her. In the literal sense, that is what they were. Compared to some of the other people in Hollywood, however, they certainly didn't feel like that big of a deal. Just kids.

Still, they didn't want to make anymore of a fuss. After all, this was a special night.


	8. Fancy

The hostess lead them over through a short hallway that lead to a smaller dining area, secluding from the general public. Simon felt a little silly. He had assumed they would just be seated in a corner, not in an entirely different part of the restaurant.

A voice could be heard crooning from in the main room. Live music wasn't uncommon in these sort of places. It definitely intensified the romantic atmosphere.

With the menus placed before them, the hostess quickly bounced away and left the two to their own devices. "I-I hope this isn't weird. I didn't think we'd be put back here." Simon missed nervously.

Jeanette shook her head, a soft smile visible over her menu. "It's lovely." She reassured him. Now that the hostess had left, he began to glance around at this smaller dining area. There were only a few tables, each with a white tablecloths and a small lantern in the middle. Gold trimming and details adorned velvety red walls. If this really was their first date, this certainly was a nice place to have it.

Simon's thoughts were once more brought back to the purple box in his pocket. Was now the right time to give it to her? Maybe this was too romantic of a setting. Maybe she would get uncomfortable.

Then, like another cosmic sign, their waitress showed up, asking about drinks and appetizers. Jeanette leaned over the table, whispering to Simon "this place is kind of pricey, Simon."

He laughed a bit and shook his head "don't worry about it, it's on me." They made quick work of ordering their drinks and some soup,and were left with some bread to tide them over, much to Jeanette's delight.

"You said Dave's been here before?" The chipette asked, her head craning to one side slightly in curiosity.

Simon nodded, swallowing a piece of bread he had been chewing on. "Yeah a few times. It's his favorite place to-" he started, but then hesitated to spit out the second half. He swallowed hard, eyes averting from the green ones that stared back at him so intently. "It's his favorite place to… go on dates."

"Oh!" Jeanette chimed, sounding a bit surprised.

"Y-yeah. I thought. Y'know since it's right here… it couldn't… hurt to try." He was sure he sounded nervous at this point. He knew with all certainty that her question wasn't meant to be prodding, but it didn't change the feeling of being under interrogation.

'Okay Si… you're being dramatic… it's just Jeanette. Kind, sweet… pretty… Jeanette…'

Another hard swallow. The waitress showing up with their soup a few seconds later was truly a blessing. Simon breathe a slight sigh of relief. After ordering some pasta and being left alone once more, the air between the two fell silent. It wasn't their usual, comfortable silence. There was a tension. He was sure it was all coming from him, but it didn't make it any less uncomfortable.

Simon's hand fiddled with the small box in his pocket. 'Just do it. She's been looking at it for so long. She'll love it'. After all, a Christmas gift wasn't necessarily romantic, right? He could just play it off like he forgot it was in his pocket and just remembered to give it to her. He was settled. Now felt like the right time. "Jeanette I-"

He was quickly interrupted by the hostess and a man entering the room. He was a shorter man, round and with a dark mustache. He had a warm smile, but it was also accompanied by a look only akin to distress. "Signor, Signorina, I hate to interrupt," he began, his thick italian accent becoming very apparent. "I am Signor Esposito. I own this establishment."

He extended his hand, giving Jeanette and Simon each a friendly shake. They smiled to him, but were nervous they had done something wrong. "How can we help you, Segnor?"

"Leah here tells me you two are musicians~" he sounded delighted, his hands pressing together in excitement. Jeanette and Simon both nodded their confirmation. "Wonderful! So much talent at such young ages!"

The pair laughed for a moment, not entirely sure where he was going with the whole thing. Finally, the hostess sighed, hanging her head a bit. "We really hate to ask, but we're desperate. Our main act for the evening had to cancel and we need someone to perform."

Simon and Jeanette looked between one another, unsure of what to say or do. Impromptu shows were more Alvin and Brittany's thing. They were just back up for the most part.

The man gave a pleading look, his brown eyes full of hope. "Please, if you'll perform, know that you will always be welcome free of charge at Bella's."

There was a long silence, Simon and Jeanette swapping glances, as if they were attempting to communicate without words. Alas, it was to no avail. Simon's shifty eyes and Jeanette's nervous grin certainly weren't the easiest to read. Even for each other.

Jeanette was the first to speak, offering them a soft smile, "could we have one moment to discuss it, please?"

"Of course!" The owner agreed. They were quick to shuffled out, leaving the pair alone to discuss. "We've never performed by ourselves, Jeanette." Simon pointed out.

"Well, not in public." She corrected. She had felt a bit of guilt for Simon paying for such a fancy dinner and this was an opportunity to dissolve that guilt. "Besides, it's not like it's a stadium. W-we'd just need to sing a few songs and be on our way."

They were the quiet ones, preferring to stay in the back and out of the public eye. The idea of getting up on stage, just the two of them was nerve wracking. Sure, they had plenty of songs up their sleeve. Simon and Jeanette had spent a good amount of time in the music room alone, playing songs just for fun. That was different. There was no way that they were ready to perform on their own.

On the other hand, it was a small crowd and a good opportunity for growth. They always seemed to have fun when it was just the two of them. Maybe that was enough to captivate an audience. If they saw how much the two chipmunks enjoyed singing together, maybe they would enjoy it too.

Simon appeared to chew on the idea for a while. He always loved singing with Jeanette, and while he was more than happy to pay for dinner, it was a nice bonus. Sure, they weren't the leads for their respective groups, but that didn't mean they couldn't put on an entertaining show. "Alright. Let's do it."

From around the corner, they could hear a giddy holler from the owner. He reappeared in an instant, practically dancing. "Thank you! From the bottom of all our hearts at Bella's, thank you!"

Simon's face flushed deeply and he chuckled a bit, feeling discomfort from the attention. Then he thought for a moment and it hit him. "Segnor, we don't know any Italian

songs."

The man gave a hearty laughed and waved off the dark haired chipmunk's concern. "Bella's is known for offering a variety of entertainment! Some Christmas songs will do just fine!"

Christmas? Now that they could do. "Do you have a guitar or a piano we could use?" Simon asked.

He gestured for the hostess to come back. "Leah, could you be a dear and ask Nick if we could borrow his guitar?" Simon assumed that was one of the band members playing with the man who was singing earlier. She quickly agreed and bounded off in the direction of the main dining room.

Simon had hoped for some sort of keyboard or a piano. Jeanette was a master on the piano and he always loved listening to her play and assumed others would too. However, that merely came down to personal preference. He really wasn't too picky. He could play guitar just fine and it would get the job done.

Moments later she returned with an acoustic guitar in her hands. "I hope this will do!"

Simon took it with a smile, "it's perfect." He strummed it a few times, trying various chords to ensure it was in tune. With a confident nod, he turned back to Jeanette and gave her a small thumbs up. "Let's do this."


	9. In The Moment

"Ladies and gentlemen!" The hostess rang out from over the microphone on stage, "We have a special Christmas treat for you tonight!"

Simon made his way onto the stage, Jeanette following closely behind with her hand tightly gripping his. She was nervous; he could see it in everything from her face, to her posture. This was one of those moments he wished he could just tell her how fantastic he was. But a crowd of people and has own nerves prevented him from acting on such desires. Instead, he opted to give her a reassuring smile and a gentle squeeze of the hand.

Simon walked up to one of the two pics that had been provided for them. He cleared his throat, giving a nervous wave to the audience. A few gasped, shocked by the sudden presence of the famous teens. "Hi guys, I'm Simon, from The Chipmunks."

He looked to Jeanette and gave a small nod of encouragement. The female moved closer to her own microphone, mimicking Simon's meek wave. "A-and I'm jeanette from The chipettes."

They could hear a few voices from the crowd, whispers of "Oh wow!" "They're so cute!", and "Where are the others?". The last one was to be expected. Even Eleanor and Theodore had done a couple of impromptu shows just for fun. Jeanette and Simon? It was unheard of and hopefully a treat for those who were present.

"Happy Christmas Eve, everyone," Jeanette started, flashing a small smile to the onlookers, "We're here to perform a few songs for you, if you'll have us."

A cheer rose from the audience, alleviating a bit of the pressure. Jeanette gave Simon a nod, letting him know it would be alright to begin playing. They had discussed it before getting on stage, deciding to stick with some of the classics for the evening. He began strumming and soft and steady tune, while Jeanette took the first verse.

 _"_ _Chestnuts roasting on an open fire…"_

her voice shook slightly with nerves, causing her to worry about the next line.

 _"_ _Jack Frost nipping at your nose~"_

A quick save on Simon's part. Jeanette relaxed slight, placing a hand on his shoulder as he continued to strum.

 _"_ _Yule-tide carols being sung by a choir... "_

They sang on in harmony, occasionally swapping adoring glances and soft grins. The audience seemed entranced, a few on the edge of their seats, other smiling brightly, and some humming along.

 _"_ _Everybody knows, a turkey and some mistletoe…"_

After a few verses they had finally settled in, the positive response from onlookers easing their anxiety. There was some sort of bliss that came with being front and center. Simon started to understand why Alvin was such a spotlight hog. That didn't mean he was going to be demanding solos anytime soon, but this moment, with one of his favorite people, would be one he surely would remember for a long time.

Jeanette began to sing alone, now comfortable enough to not need Simon to sing with her.

 _"_ _They know that Santa's on his way,_

 _He's loaded lots of toys and goodies in his sleigh…"_

Simon thought her voice was beautiful, light and floating through the room.

 _"_ _And every mother's child is gonna spy,_

 _To see if reindeer really know how to fly…"_

Once more, they came back together.

 _"_ _And so, I'm offering this simple phrase,_

 _To kids from one to ninety-two,_

 _Although it's been said, many times many ways,_

 _Merry Christmas to you~"_

The audience rose into an energetic applause, causing the pair's hearts to flutter with confidence. The support was overwhelming. After the clapping died down, Simon cleared his throat to speak again, "Thank you guys," He began, grabbing hold of Jeanette's hand. Her face flushed brightly in response. "We've got a few more songs for you tonight. We hope you enjoy."

They performed every song with passion and enthusiasm; 'Have yourself A Merry Little Christmas', 'Silver Bells', and 'White Christmas'. When it was all over the audience once again rang with applause. Simon and Jeanette lingered afterwards for a bit, talking to some of the crowd. A few had come up to them after the performance to express how much they enjoyed it.

They heard a number of different things along the lines of "you guys were great!", "It was nice hearing you guys by yourselves", and "I love the Chipmunks!" Each kind word was met with a thanks and a smile. This may have been the most relaxed they had ever been in a public setting.

However, things seemed to shift with the final person who approached them. It was a girl, most likely around their age, holding hands with someone Simon assumed was her boyfriend. "You guys were great!"

The pair appeared vaguely familiar. The taller of the two chipmunks had realized he had seen the couple around school a few times. Their names escaped him and he was sure they weren't in the same grade as him. Nonetheless, the compliment was still taken graciously. "Thanks guys! Glad you enjoyed it!"

The girl's boyfriend chimed in this time, "I was just bringing her out for a nice dinner, we didn't expect to see a show! And from some familiar faces nonetheless!" Simon and Jeanette immediately felt guilt for not knowing the names of the other two. The confusion must have been obvious because the male laughed and sheepishly rubbed the back of his head. "Sorry for not introducing ourselves. I'm Luke, this is Milly."

His girlfriend waved to accompany her introduction. "We've a grade above you guys and definitely not in any smarty pants classes. So don't feel bad for not knowing us~"

They felt relieved. They really needed to be better about being so readable. Thankfully, these two were so understanding. "It's nice to meet you!" Jeanette said, extending her hand and receiving a small shake from Milly.

"I never realized you two were a couple, you're so cute together!" Milly exclaimed. Simon's eyes quickly shifted to his left hand intertwined with Jeanette's right. Then he looked back to the couple who were almost mirroring them.

"O-oh we're not…" Simon was quick to dismiss it, out of concern that the comment would make Jeanette uncomfortable.

"I-I'm sorry!" She came back, hanging her head a bit ashamed. "I just assumed…"

"Annnnyway," Luke starter, beginning to tug his girlfriend in the opposite direction, "I'm sure you two want to return to your evening. It was nice talking to you!" Simon waved to them as they left. There was a change in the atmosphere, however. Something had shifted.

They finally returned to their meal, silence falling over them as they ate. Simon attempted to make conversation a few times, which only seemed to last for a few minutes at the most. But generally, she was quiet.

Jeanette spent most of the meal not speaking, with her gaze firmly planted in her lap and seemingly uninterested in her food.

She seemed… upset. Was it something he had said or done? Was it the girl assuming they were together? This struck a chord in him. The idea that she was so upset about someone thinking they were a couple was heartbreaking. Had he really been so wrong? Was he that bad at reading her?

After another half hour of silence, only broken with uncomfortable small talk, they finally decided it was time to leave. They gave their goodbyes to the owner and made their way back out into the street. Simon looked at his watch, realizing it was already nine thirty. How had it gotten so late?

The buses would stop running soon. If they didn't leave now he would end up having to call Dave to pick them up. As they began to walk, her looked to Jeanette, her eyes downcast and facial expression grave. Simon felt concern.

No. It wasn't concern. It was… Pain.


	10. Confessions

The walk was quiet, with Jeanette walking behind him and staring at the ground. He had peaked at her a number of times, his brows knitting together. It hurt to see her so upset, but it hurt even more to think about why.

Suddenly, after a misstep and a loose shoelace, Jeanette was sent barreling forward. Like always, Simon was there to catch her. Silvery eyes locked with green, and in that moment, his heart stopped. It was all too complicated. He wanted desperately to just tell her how he felt and rip the band-aid off. But after what had just happened, he was sure that would drive her away.

"Th-thank you…" she said, her eyes now tearing away from his face.

'This hurts…'

After a few more seconds, he finally let her go. They continued walking, the quiet between the two occasionally breaking when a car would zip by or when they would pass other people walking along and chatting. But for the most part, they were alone.

Generally, this wasn't a bad thing. Even in crowds of people, they remained in their own little world where nobody else existed. But now, Simon has never felt farther away from her.

It was unbearable. Simon sucked in a deep breath, his shaking hands clenched into fists at his side. The male stopped in his tracks, spinning on his heels and facing Jeanette. "Listen I-" he was quickly silenced by the sound of sniffling.

Jeanette rubbed at her face with her sleeve, drying tears as they fell. "I-I'm sorry…" she whimpered out. He had never felt so confused in his entire life.

Simon was quick to move closer to her and grab for her hand. However, she pulled away. The second heartbreak of the night. "Why are you so upset? Was it what that girl said? Because-"

"I-it wasn't what she said." She managed out between hiccups. If you were to look up confusion in the dictionary, Simon was sure his face in that moment would be right next to it.

"Then what is it?" He asked.

Jeanette just shook her head and backed away from him. "I-it hurts… when y-you care about someone so much…" she paused, and sucked in a puff of air. "When you care about someone a-and they're so quick to…" she wasn't speaking clearly and towards the end anything she said was inaudible. But she breathed again, mustering the courage to try and speak more clearly. "You w-were so quick to d-deny it…"

It felt as if someone had punched him in the gut. 'Simon the brain'. Yeah? He sure felt pretty stupid. "Jeanette I-"

"It's f-fine Simon. I understand… you don't need to explain it." She began to walk past him, quickly and without much warning. Before he knew it, she was practically running; bolting down the sidewalk and getting farther and farther away from him.

He shouldn't have waited so long. He should have just given her the necklace. He should have come clean about how he felt. Maybe then he could have saved her some heart ache.

But it wasn't too late. Simon pulled the box out of his pocket, glancing at it and making up his mind in an instant.

He ran after her, faster than he ever had. In his mind, it truly was now or never. Too much time had been wasted on 'what if's and 'maybe's. He only wished he had seen it sooner.

Simon's heart fluttered with every step closer. He wasn't just chasing after her, he was chasing a friendship, a partner, and that little, comfortable world they had created with each other. He left behind every doubt he had with each swift stride.

The gap was closing between them, and when he was close enough for her to finally hear his approach, she glances back at him. In that split second of distraction, she fumbled. Jeanette's body threatened to throw her forward into the concrete.

Simon was quicker; reaching out and grabbing her arm, he pulled her to safety. He wasted no time in pulling her into a tight embrace, one arm wrapped tightly around her, while his other hand rested on the back of her head.

The pair panted heavily, desperately trying to catch their breath. He could still hear her sniffling and could feel the dampness from her face sleeping through his shirt.

"I… I'm sorry…" He panted out, his chest rising and falling rapidly. Jeanette shook, whether it be from the cool, evening air or emotions, he wasn't quite sure. He pulled back slowly, looking down at her tear stained face. His thumb rubbed at the moist fur on her cheeks, trying desperately to wipe away the tears he had caused.

"I didn't deny it because I don't want to be with you," he started. This caused her to finally return his gaze. Her eyes were wide and also a bit confused. "I… I denied it because…"

Simon took a long pause. Jeanette's slender fingers played with the fabric of his sweater, as she tried to croak out enough encouragement for him to continue, "because why?"

"B-because… I wasn't sure if you'd want to be with me…" he breathed in deeply and shook his head. Simon placed his hands on her shoulders, his eyes fixated on her and unyielding. "Jeanette Miller, I adore you." His heart beat rapidly in his chest, strong and loud enough that he could hear it in his own ears. "I've… I've adored you since the moment I met you."

"Simon…" She whispered, shocked by his confession.

He shushed her for a second and gave a small, pleading look. "There's so much I wish I had said sooner,j-just let me get it out there…" Jeanette nodded in understanding, allowing him to continue. "You're my best friend. You will always be my best friend. Somewhere along the way, I'm not sure when, my feelings changed…"

Simon paused, swallowing hard and attempting to gather his thoughts. "E-every second I spend with you isn't long enough… you're beautiful and intelligent… Everything you do makes me smile… A-and when I'm close to you I feel like I'm on air…" another deep breath, "I want nothing more than to be with you."

There was a long silence and suddenly Simon was beginning to worry he had said to much. She didn't say anything, just stared at him; but her expression was unreadable. He was about to speak again, until he felt her move closer. She leaned in, placing a soft kiss on his lips.

Simon's face flushed quicker than he ever thought it could. When She finally pulled back, her cheeks were noticeably red. His face shifted into a goofy, nervous grin. "S-so… will you be my…"

"Yes." Jeanette said softly, her arms wrapping around his neck in a tight hug.

He returned the embrace, feeling like a weight had been lifted off of him. "Oh thank god… I don't think I could have finished that question without my voice cracking." He laughed. "O-oh! By the way," he pulled back for a second, pulling out the purple gift box he had been holding onto all night, "I got you a Christmas present."

Jeanette took the box, her head tilting slightly with wonder. She carefully pulled off the lid, revealing the delicate necklace she had been eyeing for so long. "Oh Simon…" she smiled softly, her fingers gently running over the beautiful jewelry.

"I know how much you wanted it… So I figured it would be the perfect gift." He reached out, grabbing the necklace from the box and gesturing for her to turn around. She happily obliged, lifting up her dark tresses to give him better access to her neck.

After making sure the necklace was in place and secure, she turned around to face him again. Jeanette's expression appeared uneasy and a bit nervous. "What's wrong?" He asked.

"I-I feel kind of silly about the gift I got you…" she sighed, her face falling a bit. Still, she reached into her purse pulling out a small, rectangular box, wrapped in blue paper with white snowflakes and a perfectly put together bow. "I… I must have rewrapped it at least five times… I wanted it to be perfect."

Simon took the box, taking a moment to admire admire the beautiful wrapping and care she had put into it. "It almost seems like a shame to unwrap it." He said honestly. Jeanette laughed and shook her head.

Without another moment to waste. He began carefully undoing the ribbon and tried his best not to rip the paper. Beneath it was a simple, black box. He removed the lid to reveal a pen. It was a steely, dark blue, with silver accents. He lifted it out of the box to read a small engraving of his name, in a beautiful cursive that he recognized as her own.

"It's perfect, Jeanette."

"I-it has refillable cartridges… so if the ink runs out you can still use it… a-and I wrote it myself and gave it to them so it was a little more personal… and-" before she could finish, he pulled her in once again, kissing her deeper than before. Simon could feel her smile against his lips.

When he finally broke the kiss, he looked at her, nothing but adoration present on his face. "I love it. Thank you."

After what felt like hours in that empty spot on the sidewalk, they finally decided to continue home. They walked, hand in hand as they always had. But this time it was different. They weren't two friend, with unrequited love on their minds. They were starting a new chapter of their lives, after hesitating to finish the final page of the last one.


End file.
